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Vacation rentals with a pool in Province of Grosseto

Find and book unique homes with a pool on Airbnb

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Popular amenities for Province of Grosseto rentals with a pool

House rentals with a pool

Top guest favorite
A serene outdoor space features a rectangular swimming pool surrounded by a lush green lawn. Four lounge chairs in soft pink are positioned nearby, offering a view of the expansive countryside and distant hills under a partly cloudy sky.
Home in Buonconvento
4.97 out of 5 average rating, 87 reviews

S.Ilaria - Private pool Villa with 2 bedrooms

AlisonRating, 5 stars1 week ago
Fabulous setting in the middle of fabulous Tuscany. The views from the house were stunning! The farmhouse itself was so charming - every detail. We enjoyed dinners on the covered patio, evening walks on the gravel road through the countryside and lounging by the pool with a glass of red wine. The setting is also the perfect location for day trips to nearby cities. We visited Montalcino, Montepulciano, Siena, Pienza and Cortona. Highly recommend!
Guest favorite
A spacious balcony offers panoramic views of the sea and distant coastline, where boats are visible in the harbor below. The vibrant blue of the water contrasts with the sky, creating a serene backdrop. Comfortable seating is arranged for relaxation while enjoying the scenery.
Home in Porto Santo Stefano
4.75 out of 5 average rating, 44 reviews

Stunning new house with amazing sea view and pool

EthanRating, 5 stars4 days ago
One of the best views you will find! Place is clean and comfortable. AC in every room and worked well. Probably the best washer dryer we had in Italy :) Incredibly responsive host. Highly recommend!
Top guest favorite
Home in Chiusdino
5 out of 5 average rating, 27 reviews

Il Camino: cosy & artfully inspired country house

MildredRating, 5 stars3 weeks ago
Thomas was so sweet and helpful. He was an absolute gentleman and wonderful host. The views were amazing. Very homey and decorated in the Tuscany style. Close to town but perfect for a quiet escape in the Tuscan countryside.
Superhost
A large swimming pool reflects the blue sky, surrounded by an expanse of green lawns and trees. Sun loungers are positioned nearby, offering space for relaxation. Rolling hills in the background create a natural setting, enhancing the tranquil atmosphere of the area.
Home in Scarlino
4.82 out of 5 average rating, 11 reviews

3 rooms in the woods, with swimming pool - Fonte di Sotto

GérardRating, 5 stars10 months ago
Margherita is very welcoming, good tips for the must-sees of the region, we had a very pleasant stay, comfortable bedding, spacious and well arranged house, a splendid swimming pool with views (about 20m long), lots of sunbed, air conditioning everywhere. So yes, the dirt road to get there may seem long sometimes but that's the price of tranquility. Only downside, the risk of having noisy neighbors on the lower or upper floor (which we had for 3 days).
Top guest favorite
A private pool is situated on a sunlit terrace, surrounded by lush greenery and rolling hills. Four lounge chairs are positioned nearby, inviting relaxation. The tranquil water of the pool reflects the surrounding natural landscape, creating a serene outdoor space.
Home in San Giovanni d'Asso
5 out of 5 average rating, 62 reviews

Country chic house in a village,private pool,wiFi

PennyRating, 5 stars2 weeks ago
Lorenzo met us on the street to walk us to the villa and showed us everything with a very warm welcome! The views are breathtaking! We found the location to be an excellent base to visit all of the surrounding towns. Having Grazia Franchini (see the host’s guidebook) prepare and serve dinner for us in the villa after a fabulous day of Brunello wine tastings was such a treat! Would definitely return to the area and stay here again but next time will set aside a day just to relax by the pool!
Guest favorite
An inviting outdoor area features a swimming pool surrounded by well-tended greenery. A spacious terrace with wooden seating overlooks the pool, offering a tranquil view of the rolling hills. Sun loungers are positioned nearby, creating a relaxing atmosphere.
Home in Grosseto
5 out of 5 average rating, 14 reviews

Tolomei Farmhouse in Stone

NatalieRating, 5 stars3 months ago
Everything is great, great place to stay with a small wellness area. We felt very comfortable!
Top guest favorite
A charming stone house is situated beside a serene swimming pool, surrounded by lush greenery. Poolside sun loungers and umbrellas are positioned along the terracotta patio, offering a relaxing outdoor space. The clear blue sky and soft clouds enhance the tranquil atmosphere.
Home in Asciano - Chiusure - Monte Oliveto Maggiore
4.96 out of 5 average rating, 182 reviews

Country House in the Crete Senesi

CharlotteRating, 5 stars3 weeks ago
We feel so lucky to of found Guido and his beautiful house. Firstly Guido could not be more helpful, so responsive, friendly and has the best recommendations! He made sure the house was spotless for our arrival, even the pool is so clean it was perfect. The house itself is stunning, stays lovely and cool in the heat but the garden is just drenched in sunshine. Guido has made sure you can bask in the sunshine by the pool or chill out in shade in the height of the afternoon. There are so many comfortable spots to sit in! The pool was lovely and refreshing when it was hot mid afternoon and looked beautiful in the evening. Tuscany is stunning, there's so much to explore - would heavily recommend a car for that. In walking distance there are a couple of very delicious restaurants and if you're feeling adventurous you can walk to the monostary nearby which is definitely worth visiting. Thank you Guido!
Superhost
An outdoor area features a swimming pool surrounded by lounge chairs and shaded by an umbrella. A vibrant pink inflatable floats in the pool, with a children's play structure nearby. A small table and chairs provide a space for relaxation within the lush greenery.
Home in Sorano
4.83 out of 5 average rating, 127 reviews

Lovely home in villa with garden and pool

JoshRating, 5 stars6 days ago
A beautiful stay in Tuscany perfect for relaxing on the property and visiting towns.

Condo rentals with a pool

Superhost
An expansive inground pool surrounded by lush greenery showcases multiple lounge chairs for relaxation. A bamboo pergola provides shade, while the landscaped grounds extend to flat grassy areas, inviting outdoor activities and enjoyment of the serene Tuscan landscape.
Condo in Montalto di Castro
4.78 out of 5 average rating, 9 reviews

Stylish Italian Apartment w/ Pool, Near Beach!

BertramRating, 5 stars7 months ago
We had a wonderful time in the apartment Mirto. Everything was thought of, we were warmly welcomed, there was a huge fruit bowl and wine. The amenities were especially great for families. Even a laundry basket was there. The outdoor area was indescribably beautiful. So much space. So much nature. This tranquility. Heavenly. We slept wonderfully. Beds are very comfortable. There are plenty of cabinets. The furnishings of all rooms are incredibly tasteful. We felt incredibly comfortable. Thank you for the wonderful time ♥️ We recommend a trip to the magical mountain village of Pitigliano, about 1 hour away.
Superhost
An outdoor swimming pool is featured, surrounded by lush greenery and trees. Poolside lounge chairs and an umbrella provide relaxation options. Soft lighting creates a serene atmosphere as dusk falls over the charming countryside, with a rustic building visible in the background.
Condo in Montepulciano
4.88 out of 5 average rating, 40 reviews

Girasole Apartment

GianmarcoRating, 5 stars1 week ago
Amazing place, staff provides great service whenever needed
Superhost
A bright living area features large windows providing views of the sea. A comfortable sofa is positioned beside a modern coffee table. A dining table is visible, complemented by a light fixture above. A fireplace adds character to the inviting space.
Condo in Porto Santo Stefano
5 out of 5 average rating, 4 reviews

Amazing Calamoresca

BarbaraRating, 5 stars21 months ago
Bright and cozy house exactly as shown in the photographs and description. Functional kitchen and spacious and well-disposed spaces. Clean and modern bathrooms. Terrace with sea view and fantastic views at every hour of the day and night, we were mesmerized! Quiet and relaxing setting within the Cala Moresca consortium that we already knew but was able to amaze us again with the well-kept and very clean common spaces for the amazing pool set in the rocks with an attached descent to the crystal clear sea. Top! Finally, a delightful and very helpful owner who made us feel at home. Absolutely repeatable.
Guest favorite
An aerial view captures the property surrounded by lush greenery and fields, featuring a central swimming pool with a circular layout. The inviting outdoor area is complemented by well-maintained hedges and cypress trees, while rustic buildings provide accommodation nearby.
Condo in Grosseto
4.83 out of 5 average rating, 30 reviews

Il Granaio apartment Il Fienile with pool.

MartinaRating, 5 stars11 months ago
We stayed a week in one of the barn houses. The property is immersed in the Maremma countryside where the peace and sounds of nature reign. A few minutes away from vegetable shops, typical products and supermarkets. The nearby beaches are easily accessible in a few minutes by car and suitable for families. Hosts have recommended beaches, restaurants, and things to do near the property. The house is simply furnished but everything is perfectly functional and functional, the garden that each apartment has is delicious, fresh and full of flowers. For us it was an ideal solution to be able to explore the area and have the privacy and tranquility we were looking for for our holidays.
Guest favorite
A saltwater swimming pool is set within a paved sun terrace, surrounded by lounge chairs and shaded by a wooden gazebo. Lush greenery and a brick wall create a serene backdrop, while the farmhouse structure is visible in the distance under clear blue skies.
Condo in Buonconvento
4.93 out of 5 average rating, 27 reviews

Relax between Siena and Valdorcia

CalvinRating, 5 stars4 days ago
I stayed at this place for 4 nights with my partner at the beginning of June 2025. It was so homely, very tidy and clean, with lots of amenities and the host was very welcoming. The views were incredible. We had a car which made visiting other places super convenient. We definitely recommend and would love to come back one day!
Guest favorite
An ancient stone building features a rustic wooden door framed by weathered walls. A vibrant cluster of pink flowers adds color to the scene, while gray clouds hover above, suggesting a tranquil atmosphere in the quaint village setting.
Condo in Bagnoli, Arcidosso
4.79 out of 5 average rating, 56 reviews

House in the small village with private pool

ChrisRating, 5 stars2 weeks ago
Quaint and cozy countryside cottage in a small welcoming village for an authentic experience. An opportunity to slow down and explore the beautiful landscape. Responsive host with a well stocked kitchen. Grocery store nearby. Walking trails everywhere and hot springs accessible with a car.
Top guest favorite
A spacious bedroom is highlighted by a decorative sunburst headboard. Soft lighting from two bedside lamps creates a gentle glow. A mirror is mounted on one wall, and a coat rack stands nearby. The tiled floor and exposed wooden beams contribute to the overall design.
Condo in Massa Marittima
5 out of 5 average rating, 43 reviews

Podere Casanovola, Il Sole apartment

MartinRating, 5 stars1 week ago
We stayed with Maria and Rodolfo for four nights and felt very, very comfortable. The beautiful house is off the road in idyllic countryside, surrounded by a park-like garden; a Shangri-La in the Maremma. The house is conveniently located for exploring the sights of the surrounding area. Maria and Rodolfo are the friendliest, most considerate and pleasant hosts you could imagine. Thank you for everything!!
Top guest favorite
A serene outdoor pool is surrounded by lush greenery, with sun umbrellas positioned around the edges. Rolling hills and a clear sky provide a scenic backdrop, offering a quiet and inviting atmosphere for relaxation.
Condo in Montieri
5 out of 5 average rating, 47 reviews

Podere Cupiano "La Costa"

LucyRating, 5 starstoday
Francesco is an excellent host. Podere Cupiano is a fantastic estate. The views are to die for. Sopratutto, the pool is amazing. Montieri is a super cute and friendly town nearby with great restaurants. You should also visit the restaurant at VIN Hotel, a ten minute walk away.

Home rentals with a private pool

The property is set in a serene countryside landscape, surrounded by lush trees and neatly arranged olive groves. A kidney-shaped swimming pool is visible within a carefully landscaped garden, providing an inviting outdoor space. The house features a simple roof and is complemented by nearby greenery.
Home in Castel del Piano
5 out of 5 average rating, 3 reviews

Il Cipresso by Interhome

StefanieRating, 5 stars1 week ago
The house was amazing, especially the area and the views. Sitting outside and using the pool in this beautiful surrounding were absolutely fantastic. It's a very wie and lovely place with a very nice pizza oven and barbecue outside. The owner are very nice and the communication was really good. We would really like to come back. Thank you for everything and also for the nice olive oil!
A shaded outdoor patio area features a wooden table and benches, surrounded by scenic views of rolling hills. The stone cottage entrance is visible through open double doors, complemented by terracotta tiles and flourishing plants.
Home in Castelnuovo di Val di Cecina
4.67 out of 5 average rating, 3 reviews

Pino di Sopra, by Interhome

MarthaRating, 5 stars24 months ago
Agrotourismo Pino di Sopra is a beautiful set of rooms in a peaceful part of Tuscany off the beaten track. The house is set up as two apartments and two double rooms, so perfect for two families sharing or a group of friends where you can all have your own space. The pool is large and suitable for kids and adults alike. I would highly recommend staying here. Our only negative was that the host told us we had to communicate off platform with the key holders (owners) which I was uncomfortable with. I had trouble getting in touch with the key holders and the hosts did not respond to my messages for assistance or offer any support with this. Once I made contact via SMS the owners were very helpful and responsive. It there was undue stress in the lead up to our trip.
A rectangular swimming pool is surrounded by a stone patio and several lounge chairs. Lush greenery and trees are visible in the background under a clear blue sky.
Home in Lago di Bolsena
4.32 out of 5 average rating, 19 reviews

Casale Vitello by Interhome

ThibaultRating, 5 stars7 months ago
We are very happy with this stay and we had a lovely time with very good exchanges.
Home in Castiglione d'Orcia
4.67 out of 5 average rating, 30 reviews

Casa Frati by Interhome

JoJoRating, 5 stars3 days ago
Overall the location and charm of the property were stunning. Spacious bedrooms and living areas (beware uneven flooring, to be expected in an old farmhouse, my elderly father struggled). NOTE: we have not been asked for a cash deposit with Airbnb before and were surprised when a man came about 3 hours after we arrived to collect €400 cash. He spoke no English and used his phone to call someone who could speak to me. The host had not said he would be coming, or who he was. I contacted Airbnb support who said I could pay through the resolution centre. As others mentioned, there were no oil, salt, pepper etc, although a few dishwasher tablets. The jacuzzi and sauna work with tokens for €8 each. Didn’t use so not sure how long you get. BUT, this is a stunning property with unbeatable views in the heart of Tuscany, tucked away on a hillside down a gravel track. Would definitely book again. Pool is pristine, towels spotless, beds comfortable.
Home in Roccalbegna
4.5 out of 5 average rating, 4 reviews

Meridiana by Interhome

PhilippeRating, 5 stars21 months ago
Quality accommodation in a beautiful environment!
Home in Radicofani
4.86 out of 5 average rating, 7 reviews

Val d'Orcia by Interhome

AmandaRating, 5 stars20 months ago
Awesome property! Super responsive host!
A spacious dining area features a wooden table adorned with a vase of flowers and a bowl of lemons. Soft natural light enters through large windows, highlighting a comfortable living space with a sofa in the background. Exposed wooden beams add a warm touch to the ceiling.
Home in Roccastrada
4.93 out of 5 average rating, 14 reviews

Casa la Selvolina, by Interhome

JonasRating, 5 stars1 month ago
Very Kind and lovely guys, quiet and relaxing area. I loved it
A serene outdoor area features a rectangular swimming pool surrounded by paved terrace and sun loungers. Shade is provided by umbrellas near the pool. Lush greenery and trees line the property, with distant hills visible under a clear blue sky.
Home in Poggioferro

Villa al Sole by Interhome

MartinRating, 5 stars9 months ago
The house corresponded to the description in every way. It was exactly like the pictures. The landlord was very nice. He was always available and took care of everything. Everything top 👍👍👍👍 5 stars ⭐️⭐️⭐️⭐️⭐️

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